Batchelor become the batchlorette

I was getting married, a cause for celebration undoubtedly, but also a cause for regret. Regret for all the potential I was leaving behind with my single life. All the things that I could have done and all the people I could have done it with. I loved my fiancée, Gina, very much; she was gorgeous, kind-hearted and generous, but also very traditional in her ways and morally straight-laced. It had taken all my powers of persuasion and a shiny diamond engagement ring simply to persuade Gina to sleep with me before we were married and that was the limit of our sex life, nothing more exciting or un… Читать далее

Креатор: redthongthong 3 мес. назад 1

A threesome with something extra

Jeff worked as a bartender. He had been in the business for 10 years and figured he'd seen everything. Working in a small seaside town in New England had its ups and downs like anything else. Busy summers, slow winters, but a decent living all around, and even though the hours were long and late, there were fringe benefits to be had. Plenty of free booze, and the frequent pussy to be found. Jeff smiled remembering his younger days when he'd fuck 2-3 different women a week. It had led to a few problems, and Jeff had quickly adopted the motto "Don't fish off the company pier." Nowadays, at 33,… Читать далее

Креатор: redthongthong 1 год назад 9

I had no idea what I wanted.

There I was, one week before the end of high school. Going to college in the fall. Nice car, good family, friends. I had it all. So, what was I doing on my hands and knees in a video booth on the wrong side of town, dressed as a cheerleader with a cock in each hand, one in my ass and one buried in my throat? It had all started a few months ago. I was locked out of my house in the pouring rain, and I went over to our neighbor’s to see if I could hang out with him until my parents got home. He was a cool guy, single, mid 30’s, worked for a software company, and drove a nice car. Had bought me b… Читать далее

Креатор: redthongthong 1 год назад 2

My sissy fantasy cums true

Before I get into the story, let me give you a little background info. I had considered myself to be straight for most of life. It was until just before I graduated high school that I discovered I may not be as straight as I thought. I got curious while I was jerking off one day, and I ended up cumming to a video of a crossdresser getting ass fucked by a giant cock. That was the straw that broke the camels back. Before I knew it I was hooked. Twinks, shemales, crossdressers, pegging...pretty much every category but straight porn. My absolute favorite category though was anything involving a s… Читать далее

Креатор: redthongthong 1 год назад 12

WTF Happened Last Night. My ass is sore.

Oh my GOD I'm so hungover. I creak my eyes creak open, and immediately regret doing so. Everything hurts. My head is pounding. My mouth tastes like something died in it. I try to sit up, pause, flop back onto the couch. At least I've got blanket. Wait... I'm not in my bed. Where the fuck am I? I rub the back of my hand over my eyes, feeling a weird, heavy texture. My fingers catch in my scratchy wig, and my ears feel heavy- Oh, that's right. It's fucking Halloween. So I'm still dressed like a schoolgirl. I run my hands down my body, under this stupid scratchy blanket. Yup. Tubetop, check. M… Читать далее

Креатор: redthongthong 1 год назад 4

Busted by step daughter in her panties

I went through forty-five years of my life as a single man, no one to answer to but myself. I watched my friends marry, have c***dren, and get divorced. I kept hearing the same old stories, 'money problems', 'she wasn't the same in bed after the k**s came', 'we are too tired because of the k**s', and the best of all 'we fight too much over money and the k**s'. I would just listen and laugh in my head at them. Then I met Emily. Emily was just your average sized woman on the outside, size 12 full figured, but she carried it well. It was her big boned body frame rather than just added weight. She… Читать далее

Креатор: redthongthong 1 год назад 18

Dressing for party leads me down a path

My name is Jason, and I suppose it all started when I was 21, in my third year of college. My friends and I were going to a theme party where the girls would dress as guys and the guys as girls. I was studying in a city in California, and it was a warmer than usual May, so we all decided to wear skimpy dresses, wigs and makeup. To avoid an awkward situation, we agreed to go to buy our outfits together; I got a black cocktail dress that went down to my knees with a slit almost up to my waist, and some black lace panties - I don't know why, but I just thought it would be weird to have men's unde… Читать далее

Креатор: redthongthong 1 год назад 6

Blind Date at the Drive-In

As the two siblings got older, Karen's idea of having fun with a crossdressing brother changed. Ever since she began dating, she thought it would be amusing to see how her "little sister" handled boys too. She knew he could be dressed up and made up realistically enough to fool a boy up close, and wondered if Kim would actually like it. An unformed thought came to her: if he did like it, perhaps that mean he wants to become a girl, or that he should become a girl but doesn’t know it yet. Dressing him up and setting him up one-on-one with a guy would be an interesting way to test her theory. S… Читать далее

Креатор: redthongthong 1 год назад 7

tables turned blackmailer to sissy

I make a lot of money from gay men. Specifically closeted men. Married men. It's easy. I go online, send them a few pics I found on the internet, and get them salivating. There are always plenty of them, faceless accounts pile on asking for a quick suck or fuck, bottom or top, whatever their fancy. I get the blood flowing, tell them what I'll do for/to them with a few cut and paste messages. The guys who like to dress up like sissy girls are the best. I get them to send me a face pic with their mouth open, ahegao style, begging for it. Pathetic. At this point, I have them. Everything change… Читать далее

Креатор: redthongthong 2 года назад 3

Halloween crossdresser awakening.

As I d****d the sheer pantyhose onto my legs to finish off my Halloween costume, preparing for a night of cock sucking and bottoming at the annual Halloween men's only orgy (my wife Amber going to her own annual girls only Halloween orgy), I couldn't help but reminisce about the day I realized I loved wearing pantyhose, loved sucking cock and was a natural bottom. It was thirty years ago. The year was 1989. I was eighteen. I was straight. I was the starting wide receiver on my high school football team. I was dating a knockout cheerleader, Amber (whom I eventually married), who was a kin… Читать далее

Креатор: redthongthong 2 года назад 13

My daughter’s sissy

How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it. I suppose I shouldn't have let myself get into this situation. I shouldn't ever have had an affair but my sex life with my wife was dead and I still had needs that couldn't real… Читать далее

Креатор: redthongthong 2 года назад 8

Be careful what you wish for.

It all started when my wife (Staci) and I had a conversation about how comfortable women's clothes looked and we both laughed and I boldly said, "I would wear women's panties and satin pajamas because they look really comfortable." Now keep in mind that I have always had an affinity for women's clothing, so when she was ok with it, naturally, I was super excited. Anyway, we started talking and decided to order some lingerie for me online to sleep in. We ended up buying a satin and lace short and top set. I was disappointed when it came in. It was very cheaply made and quickly broke. Staci and… Читать далее

Креатор: redthongthong 2 года назад 10

Finding the partner I need.

I was 18 when I first had sex with a man. This is the story…. I am a very hot looking guy. I say that knowing that some may consider me vain, or arrogant, but over the years I have had so many women and men tell me how fine I am, that I know it is true. I am 35, blond and blue eyed, 6’1,” 180lbs, with a tan athletic body and a 7″ beautiful cock. I have been dressing up as a sexy girl ever since I was 18 years old and had my first experience with a man. The following is how it all started The summer of my 18th year was beautiful and warm. I remember the wild high school parties outside on warm… Читать далее

Креатор: redthongthong 2 года назад 6

Sissy fantasy to reality

Like the majority of my stories, this one begins with alcohol and a hotel room. But really it begins several months before that. Ever since I was 18 I had been dressing up in some way, starting off with just wearing panties from time to time. Soon I ordered a butt plug and some lube online, and would watch porn imagining I was the one taking those big cocks. It was only when I turned 19 though that I really got serious about it - having just started university, I was one of the only guys on a course full of girls, and spent my time in lectures alternating between fantasising about sleeping wit… Читать далее

Креатор: redthongthong 2 года назад 1

My start as a camgurl part 2

How had I ended up in this situation? Sure I was going to need to make ends meet, but I could find a normal job couldn't I? was I this desperate? Perhaps desperate wasn't the right word, just over a month ago I had started out camming as a bit of fun, to maybe make a few pounds while I masturbated, which was going to do regardless of being on cam. And here I was, hairless, in a bra and thong, was I OK with this? As overwhelming as the situation was, I looked down at myself, and staring over the hard nipples inside the empty cups of my ex-girlfriend's bra, to my still very stiff, throbbing and… Читать далее

Креатор: redthongthong 2 года назад 2

My start as a camgurl part 1

Back in January 2020 I guess I was lucky, I did have a regular job although the pay was miserable and I did have my own place. On my wage all I could afford was a miserable bedsit in a neglected part of town, but on the upside I didn't have to flat share and it worked well enough for me. The western world was caught napping when Covid hit, and unprecedented measures were suddenly imposed. London locked down and we were told to stay home, a furlough scheme was launched to make sure there was no mass unemployment and companies that were forced to cease trading could continue to pay staff. The c… Читать далее

Креатор: redthongthong 2 года назад 2